# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jui-Hsien Huang' _publ_contact_author_email juihuang@cc.ncue.edu.tw loop_ _publ_author_name 'Jui-Hsien Huang' 'Jia-Wei Hsu' 'Yu-Chun Lin' 'Ching-Sheng Hsiao' A.Datta 'Chia-Her Lin' 'Jing-Cherng Tsai' data_ray3071_0m _database_code_depnum_ccdc_archive 'CCDC 867477' #TrackingRef 'cpd 5---ray3071_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H43 Cl N6 Zr' _chemical_formula_sum 'C24 H43 Cl N6 Zr' _chemical_formula_weight 542.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.384(3) _cell_length_b 9.8710(18) _cell_length_c 18.687(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.323(9) _cell_angle_gamma 90.00 _cell_volume 2661.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4537 _cell_measurement_theta_min 1.48 _cell_measurement_theta_max 28.760 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.536 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5327 _exptl_absorpt_correction_T_max 0.7738 _exptl_absorpt_process_details 'Sadabs Version 2008/1' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 45256 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.85 _reflns_number_total 6956 _reflns_number_gt 5602 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+1.0411P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6956 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0475 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.16945(15) 0.0773(2) 0.71948(13) 0.0337(5) Uani 1 1 d . . . H1A H 0.2098 0.0891 0.7727 0.051 Uiso 1 1 calc R . . H1B H 0.2073 0.0740 0.6868 0.051 Uiso 1 1 calc R . . H1C H 0.1346 -0.0075 0.7143 0.051 Uiso 1 1 calc R . . C2 C 0.10192(13) 0.1959(2) 0.69548(11) 0.0264(4) Uani 1 1 d . . . C3 C 0.03262(15) 0.1711(2) 0.61537(12) 0.0337(5) Uani 1 1 d . . . H3A H -0.0061 0.0926 0.6162 0.050 Uiso 1 1 calc R . . H3B H 0.0662 0.1534 0.5803 0.050 Uiso 1 1 calc R . . H3C H -0.0067 0.2512 0.5982 0.050 Uiso 1 1 calc R . . C4 C -0.10697(16) 0.6595(2) 0.84163(14) 0.0389(5) Uani 1 1 d . . . H4A H -0.1254 0.7086 0.7931 0.058 Uiso 1 1 calc R . . H4B H -0.0411 0.6758 0.8701 0.058 Uiso 1 1 calc R . . H4C H -0.1440 0.6912 0.8717 0.058 Uiso 1 1 calc R . . C5 C -0.22314(14) 0.4897(3) 0.78395(13) 0.0378(5) Uani 1 1 d . . . H5A H -0.2595 0.5258 0.8136 0.057 Uiso 1 1 calc R . . H5B H -0.2351 0.3924 0.7757 0.057 Uiso 1 1 calc R . . H5C H -0.2410 0.5361 0.7346 0.057 Uiso 1 1 calc R . . C6 C -0.09661(16) 0.4400(3) 0.90205(12) 0.0384(5) Uani 1 1 d . . . H6A H -0.0386 0.4788 0.9382 0.046 Uiso 1 1 calc R . . H6B H -0.1462 0.4518 0.9240 0.046 Uiso 1 1 calc R . . C7 C -0.08326(14) 0.2927(2) 0.89041(12) 0.0335(5) Uani 1 1 d . . . C8 C -0.08627(15) 0.1722(3) 0.92552(13) 0.0433(6) Uani 1 1 d . . . H8 H -0.1062 0.1587 0.9677 0.052 Uiso 1 1 calc R . . C9 C -0.05385(15) 0.0710(3) 0.88676(13) 0.0401(6) Uani 1 1 d . . . H9 H -0.0482 -0.0231 0.8980 0.048 Uiso 1 1 calc R . . C10 C -0.03228(13) 0.1353(2) 0.82997(11) 0.0284(4) Uani 1 1 d . . . C11 C 0.00456(14) 0.09651(19) 0.76853(12) 0.0289(4) Uani 1 1 d . . . H11A H -0.0469 0.0689 0.7219 0.035 Uiso 1 1 calc R . . H11B H 0.0482 0.0196 0.7855 0.035 Uiso 1 1 calc R . . C12 C 0.15613(14) 0.3260(2) 0.69633(13) 0.0335(5) Uani 1 1 d . . . H12A H 0.1131 0.4027 0.6816 0.050 Uiso 1 1 calc R . . H12B H 0.1892 0.3176 0.6602 0.050 Uiso 1 1 calc R . . H12C H 0.2009 0.3412 0.7478 0.050 Uiso 1 1 calc R . . C15 C -0.05338(15) 0.5702(2) 0.56271(12) 0.0326(5) Uani 1 1 d . . . H15A H 0.0133 0.5688 0.5719 0.049 Uiso 1 1 calc R . . H15B H -0.0863 0.6081 0.5120 0.049 Uiso 1 1 calc R . . H15C H -0.0752 0.4776 0.5653 0.049 Uiso 1 1 calc R . . C16 C -0.04557(16) 0.8035(2) 0.61167(13) 0.0376(5) Uani 1 1 d . . . H16A H -0.0560 0.8621 0.6503 0.056 Uiso 1 1 calc R . . H16B H -0.0839 0.8347 0.5607 0.056 Uiso 1 1 calc R . . H16C H 0.0200 0.8070 0.6167 0.056 Uiso 1 1 calc R . . C17 C -0.17616(14) 0.6590(2) 0.60981(13) 0.0362(5) Uani 1 1 d . . . H17A H -0.1965 0.5675 0.6171 0.054 Uiso 1 1 calc R . . H17B H -0.2102 0.6893 0.5576 0.054 Uiso 1 1 calc R . . H17C H -0.1883 0.7211 0.6461 0.054 Uiso 1 1 calc R . . C18 C -0.07201(13) 0.6573(2) 0.62322(11) 0.0263(4) Uani 1 1 d . . . C19 C 0.05578(14) 0.6870(2) 0.74836(12) 0.0311(4) Uani 1 1 d . . . H19A H 0.0301 0.7762 0.7548 0.037 Uiso 1 1 calc R . . H19B H 0.1008 0.7017 0.7220 0.037 Uiso 1 1 calc R . . C20 C 0.10477(13) 0.6266(2) 0.82496(11) 0.0259(4) Uani 1 1 d . . . C21 C 0.16708(14) 0.6833(2) 0.88937(12) 0.0316(5) Uani 1 1 d . . . H21 H 0.1864 0.7753 0.8961 0.038 Uiso 1 1 calc R . . C22 C 0.19699(14) 0.5785(2) 0.94380(12) 0.0317(5) Uani 1 1 d . . . H22 H 0.2414 0.5865 0.9938 0.038 Uiso 1 1 calc R . . C23 C 0.15026(13) 0.4629(2) 0.91145(11) 0.0260(4) Uani 1 1 d . . . C25 C 0.16141(14) 0.3248(2) 0.94616(11) 0.0303(4) Uani 1 1 d . . . H25A H 0.2013 0.3310 1.0005 0.036 Uiso 1 1 calc R . . H25B H 0.1000 0.2909 0.9440 0.036 Uiso 1 1 calc R . . C26 C 0.29741(14) 0.2684(3) 0.91500(13) 0.0398(5) Uani 1 1 d . . . H26A H 0.3358 0.2717 0.9692 0.060 Uiso 1 1 calc R . . H26B H 0.2960 0.3581 0.8922 0.060 Uiso 1 1 calc R . . H26C H 0.3236 0.2026 0.8888 0.060 Uiso 1 1 calc R . . C27 C 0.20525(16) 0.0917(2) 0.93979(13) 0.0404(5) Uani 1 1 d . . . H27A H 0.2309 0.0273 0.9125 0.061 Uiso 1 1 calc R . . H27B H 0.1423 0.0639 0.9348 0.061 Uiso 1 1 calc R . . H27C H 0.2443 0.0932 0.9939 0.061 Uiso 1 1 calc R . . Cl1 Cl -0.16082(3) 0.30788(5) 0.64801(3) 0.03021(11) Uani 1 1 d . . . N1 N 0.05350(10) 0.21797(16) 0.75227(8) 0.0223(3) Uani 1 1 d . . . H1 H 0.1019 0.2282 0.7955 0.027 Uiso 1 1 d . . . N2 N -0.05008(11) 0.27114(18) 0.83229(9) 0.0270(4) Uani 1 1 d . . . N3 N -0.12265(11) 0.51217(18) 0.82658(9) 0.0290(4) Uani 1 1 d . . . N4 N 0.09180(10) 0.49119(16) 0.83746(9) 0.0237(3) Uani 1 1 d . . . N5 N -0.01990(11) 0.59957(15) 0.70087(9) 0.0231(3) Uani 1 1 d . . . N6 N 0.20269(11) 0.22740(18) 0.90714(9) 0.0300(4) Uani 1 1 d . . . Zr1 Zr -0.036450(11) 0.416716(18) 0.752789(10) 0.01964(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0359(11) 0.0284(11) 0.0402(12) -0.0020(9) 0.0175(10) 0.0066(9) C2 0.0302(10) 0.0211(10) 0.0312(10) -0.0025(8) 0.0149(8) 0.0018(8) C3 0.0431(12) 0.0301(11) 0.0292(11) -0.0023(9) 0.0144(9) 0.0017(9) C4 0.0370(12) 0.0389(13) 0.0466(13) -0.0134(11) 0.0218(10) 0.0026(10) C5 0.0231(10) 0.0499(15) 0.0428(13) -0.0033(11) 0.0145(9) 0.0023(9) C6 0.0363(11) 0.0557(16) 0.0290(11) -0.0013(10) 0.0186(9) 0.0048(10) C7 0.0264(10) 0.0477(14) 0.0291(11) 0.0058(10) 0.0131(9) 0.0005(9) C8 0.0338(12) 0.0616(17) 0.0404(13) 0.0189(12) 0.0206(10) 0.0017(11) C9 0.0339(11) 0.0421(14) 0.0441(13) 0.0178(11) 0.0134(10) -0.0039(10) C10 0.0225(9) 0.0288(10) 0.0311(11) 0.0058(9) 0.0060(8) -0.0048(8) C11 0.0305(10) 0.0196(10) 0.0345(11) 0.0014(8) 0.0086(9) -0.0035(8) C12 0.0346(11) 0.0278(11) 0.0464(13) -0.0045(10) 0.0246(10) -0.0037(9) C15 0.0379(11) 0.0312(12) 0.0284(10) 0.0005(9) 0.0112(9) 0.0027(9) C16 0.0480(13) 0.0251(11) 0.0374(12) 0.0043(9) 0.0118(10) -0.0041(10) C17 0.0307(11) 0.0353(12) 0.0421(13) 0.0073(10) 0.0121(9) 0.0081(9) C18 0.0295(10) 0.0215(10) 0.0290(10) 0.0035(8) 0.0119(8) 0.0014(8) C19 0.0297(10) 0.0231(10) 0.0385(12) 0.0000(9) 0.0094(9) -0.0054(8) C20 0.0232(9) 0.0236(10) 0.0335(11) -0.0051(8) 0.0132(8) -0.0050(7) C21 0.0304(10) 0.0306(11) 0.0354(11) -0.0108(9) 0.0135(9) -0.0115(8) C22 0.0287(10) 0.0409(12) 0.0252(10) -0.0099(9) 0.0090(8) -0.0082(9) C23 0.0230(9) 0.0315(11) 0.0239(9) -0.0048(8) 0.0086(8) -0.0032(8) C25 0.0264(10) 0.0395(12) 0.0220(9) -0.0007(9) 0.0046(8) -0.0034(9) C26 0.0260(10) 0.0478(14) 0.0442(13) -0.0017(11) 0.0104(10) 0.0021(10) C27 0.0371(12) 0.0385(13) 0.0373(12) 0.0103(10) 0.0026(10) 0.0026(10) Cl1 0.0259(2) 0.0303(3) 0.0288(2) -0.0006(2) 0.00237(19) -0.00712(19) N1 0.0218(7) 0.0210(8) 0.0236(8) -0.0014(6) 0.0074(6) -0.0025(6) N2 0.0250(8) 0.0317(9) 0.0253(8) 0.0026(7) 0.0102(7) -0.0010(7) N3 0.0244(8) 0.0350(10) 0.0307(9) -0.0040(8) 0.0133(7) 0.0012(7) N4 0.0216(7) 0.0238(8) 0.0264(8) -0.0034(7) 0.0093(6) -0.0035(6) N5 0.0237(8) 0.0199(8) 0.0266(8) -0.0012(6) 0.0100(7) 0.0002(6) N6 0.0257(8) 0.0319(10) 0.0290(9) 0.0017(7) 0.0051(7) 0.0002(7) Zr1 0.01861(9) 0.01972(9) 0.02133(10) -0.00194(7) 0.00785(7) -0.00239(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.526(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.509(2) . ? C2 C3 1.526(3) . ? C2 C12 1.528(3) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 N3 1.485(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 N3 1.489(3) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.495(3) . ? C6 N3 1.505(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.367(3) . ? C7 N2 1.368(3) . ? C8 C9 1.422(4) . ? C8 H8 0.9500 . ? C9 C10 1.373(3) . ? C9 H9 0.9500 . ? C10 N2 1.372(3) . ? C10 C11 1.496(3) . ? C11 N1 1.502(2) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C15 C18 1.525(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C18 1.535(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.533(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 N5 1.505(2) . ? C19 N5 1.473(2) . ? C19 C20 1.491(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.371(3) . ? C20 N4 1.384(3) . ? C21 C22 1.411(3) . ? C21 H21 0.9500 . ? C22 C23 1.372(3) . ? C22 H22 0.9500 . ? C23 N4 1.391(2) . ? C23 C25 1.493(3) . ? C25 N6 1.477(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 N6 1.470(3) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 N6 1.467(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? Cl1 Zr1 2.4590(6) . ? N1 Zr1 2.4027(16) . ? N1 H1 0.8940 . ? N2 Zr1 2.1289(16) . ? N3 Zr1 2.4120(16) . ? N4 Zr1 2.1837(15) . ? N5 Zr1 2.1060(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 111.45(16) . . ? N1 C2 C1 110.84(16) . . ? C3 C2 C1 109.70(17) . . ? N1 C2 C12 105.81(15) . . ? C3 C2 C12 109.77(17) . . ? C1 C2 C12 109.18(17) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N3 C4 H4A 109.5 . . ? N3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N3 C5 H5A 109.5 . . ? N3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 N3 109.24(17) . . ? C7 C6 H6A 109.8 . . ? N3 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? N3 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C8 C7 N2 109.3(2) . . ? C8 C7 C6 138.3(2) . . ? N2 C7 C6 112.03(18) . . ? C7 C8 C9 106.89(19) . . ? C7 C8 H8 126.6 . . ? C9 C8 H8 126.6 . . ? C10 C9 C8 106.9(2) . . ? C10 C9 H9 126.6 . . ? C8 C9 H9 126.6 . . ? N2 C10 C9 108.9(2) . . ? N2 C10 C11 114.05(17) . . ? C9 C10 C11 137.1(2) . . ? C10 C11 N1 107.50(16) . . ? C10 C11 H11A 110.2 . . ? N1 C11 H11A 110.2 . . ? C10 C11 H11B 110.2 . . ? N1 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C15 H15A 109.5 . . ? C18 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C18 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C18 C16 H16A 109.5 . . ? C18 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C18 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C18 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N5 C18 C15 109.10(16) . . ? N5 C18 C16 114.40(17) . . ? C15 C18 C16 107.38(17) . . ? N5 C18 C17 109.76(16) . . ? C15 C18 C17 109.86(17) . . ? C16 C18 C17 106.24(17) . . ? N5 C19 C20 112.01(16) . . ? N5 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? N5 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C21 C20 N4 110.11(18) . . ? C21 C20 C19 130.27(19) . . ? N4 C20 C19 119.58(17) . . ? C20 C21 C22 106.71(19) . . ? C20 C21 H21 126.6 . . ? C22 C21 H21 126.6 . . ? C23 C22 C21 107.60(18) . . ? C23 C22 H22 126.2 . . ? C21 C22 H22 126.2 . . ? C22 C23 N4 109.24(18) . . ? C22 C23 C25 127.15(18) . . ? N4 C23 C25 123.54(17) . . ? N6 C25 C23 112.58(16) . . ? N6 C25 H25A 109.1 . . ? C23 C25 H25A 109.1 . . ? N6 C25 H25B 109.1 . . ? C23 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? N6 C26 H26A 109.5 . . ? N6 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N6 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N6 C27 H27A 109.5 . . ? N6 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N6 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C11 N1 C2 115.58(15) . . ? C11 N1 Zr1 108.73(11) . . ? C2 N1 Zr1 123.10(11) . . ? C11 N1 H1 103.1 . . ? C2 N1 H1 101.1 . . ? Zr1 N1 H1 101.8 . . ? C7 N2 C10 108.11(17) . . ? C7 N2 Zr1 127.11(15) . . ? C10 N2 Zr1 124.64(13) . . ? C4 N3 C5 108.51(17) . . ? C4 N3 C6 108.26(17) . . ? C5 N3 C6 108.64(17) . . ? C4 N3 Zr1 113.92(12) . . ? C5 N3 Zr1 108.09(12) . . ? C6 N3 Zr1 109.31(12) . . ? C20 N4 C23 106.31(16) . . ? C20 N4 Zr1 110.48(12) . . ? C23 N4 Zr1 139.64(13) . . ? C19 N5 C18 113.84(15) . . ? C19 N5 Zr1 114.90(12) . . ? C18 N5 Zr1 131.26(12) . . ? C27 N6 C26 109.10(17) . . ? C27 N6 C25 110.08(17) . . ? C26 N6 C25 110.65(17) . . ? N5 Zr1 N2 163.12(6) . . ? N5 Zr1 N4 79.74(6) . . ? N2 Zr1 N4 90.27(6) . . ? N5 Zr1 N1 122.41(6) . . ? N2 Zr1 N1 69.40(6) . . ? N4 Zr1 N1 84.32(6) . . ? N5 Zr1 N3 96.14(6) . . ? N2 Zr1 N3 69.99(6) . . ? N4 Zr1 N3 89.54(6) . . ? N1 Zr1 N3 138.85(6) . . ? N5 Zr1 Cl1 101.11(5) . . ? N2 Zr1 Cl1 91.31(5) . . ? N4 Zr1 Cl1 168.93(4) . . ? N1 Zr1 Cl1 85.99(4) . . ? N3 Zr1 Cl1 101.29(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.85 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.572 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.069 # Attachment 'cpd 6--- ray402_0m.cif' data_ray402_0m _database_code_depnum_ccdc_archive 'CCDC 867478' #TrackingRef 'cpd 6--- ray402_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H38 N6 S Zr' _chemical_formula_sum 'C23 H38 N6 S Zr' _chemical_formula_weight 521.87 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4590(6) _cell_length_b 26.1531(16) _cell_length_c 10.9676(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.209(3) _cell_angle_gamma 90.00 _cell_volume 2562.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 148(2) _cell_measurement_reflns_used 4551 _cell_measurement_theta_min 2.656 _cell_measurement_theta_max 29.470 _exptl_crystal_description columnar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.532 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.826 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 148(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 36264 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 29.47 _reflns_number_total 7075 _reflns_number_gt 5080 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+0.6660P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7075 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zr1 Zr 0.41066(2) 0.135040(8) 0.27005(2) 0.02005(7) Uani 1 1 d . . . S1 S 0.19519(7) 0.06708(2) 0.14887(6) 0.02614(13) Uani 1 1 d . . . N1 N 0.5197(2) 0.20707(7) 0.27581(19) 0.0256(4) Uani 1 1 d . . . N2 N 0.2220(2) 0.20431(8) 0.16382(19) 0.0274(4) Uani 1 1 d . . . N3 N 0.6399(2) 0.12114(7) 0.35028(19) 0.0246(4) Uani 1 1 d . . . N4 N 0.3977(2) 0.10729(7) 0.06968(18) 0.0220(4) Uani 1 1 d . . . N5 N 0.2036(2) 0.06417(7) -0.09381(18) 0.0251(4) Uani 1 1 d . . . N6 N 0.3314(2) 0.13005(8) 0.42484(19) 0.0278(4) Uani 1 1 d . . . C1 C 0.5065(3) 0.11213(9) 0.0059(2) 0.0225(5) Uani 1 1 d . . . C2 C 0.5739(3) 0.15941(10) 0.0068(2) 0.0297(5) Uani 1 1 d . . . H2 H 0.5412 0.1883 0.0428 0.036 Uiso 1 1 calc R . . C3 C 0.6889(3) 0.16449(11) -0.0448(3) 0.0367(6) Uani 1 1 d . . . H3 H 0.7355 0.1968 -0.0424 0.044 Uiso 1 1 calc R . . C4 C 0.7363(3) 0.12341(11) -0.0995(3) 0.0389(7) Uani 1 1 d . . . H4 H 0.8143 0.1274 -0.1354 0.047 Uiso 1 1 calc R . . C5 C 0.6690(3) 0.07616(10) -0.1018(3) 0.0351(6) Uani 1 1 d . . . H5 H 0.7008 0.0476 -0.1398 0.042 Uiso 1 1 calc R . . C6 C 0.5551(3) 0.07038(9) -0.0485(2) 0.0290(5) Uani 1 1 d . . . H6 H 0.5103 0.0378 -0.0493 0.035 Uiso 1 1 calc R . . C7 C 0.2736(2) 0.07943(8) 0.0278(2) 0.0219(5) Uani 1 1 d . . . C8 C 0.4574(3) 0.25114(9) 0.2128(2) 0.0302(5) Uani 1 1 d . . . C9 C 0.5679(3) 0.28044(10) 0.1920(3) 0.0361(6) Uani 1 1 d . . . H9 H 0.5556 0.3128 0.1506 0.043 Uiso 1 1 calc R . . C10 C 0.7045(3) 0.25294(10) 0.2446(3) 0.0355(6) Uani 1 1 d . . . H10 H 0.8008 0.2635 0.2451 0.043 Uiso 1 1 calc R . . C11 C 0.6703(3) 0.20807(9) 0.2945(2) 0.0283(5) Uani 1 1 d . . . C12 C 0.7521(3) 0.16004(10) 0.3516(3) 0.0333(6) Uani 1 1 d . . . H12A H 0.8146 0.1483 0.3003 0.040 Uiso 1 1 calc R . . H12B H 0.8181 0.1664 0.4412 0.040 Uiso 1 1 calc R . . C13 C 0.2949(3) 0.25600(10) 0.1935(3) 0.0356(6) Uani 1 1 d . . . H13A H 0.2479 0.2798 0.1214 0.043 Uiso 1 1 calc R . . H13B H 0.2808 0.2700 0.2726 0.043 Uiso 1 1 calc R . . C14 C 0.1670(3) 0.19827(10) 0.0211(2) 0.0374(6) Uani 1 1 d . . . H14A H 0.0922 0.2247 -0.0175 0.056 Uiso 1 1 calc R . . H14B H 0.1214 0.1644 -0.0014 0.056 Uiso 1 1 calc R . . H14C H 0.2510 0.2017 -0.0119 0.056 Uiso 1 1 calc R . . C15 C 0.0898(3) 0.20266(11) 0.2072(3) 0.0417(7) Uani 1 1 d . . . H15A H 0.0400 0.1694 0.1849 0.063 Uiso 1 1 calc R . . H15B H 0.0201 0.2299 0.1646 0.063 Uiso 1 1 calc R . . H15C H 0.1217 0.2075 0.3010 0.063 Uiso 1 1 calc R . . C16 C 0.2261(3) 0.08912(10) -0.2050(2) 0.0315(6) Uani 1 1 d . . . H16A H 0.2917 0.0680 -0.2372 0.047 Uiso 1 1 calc R . . H16B H 0.2723 0.1227 -0.1793 0.047 Uiso 1 1 calc R . . H16C H 0.1293 0.0934 -0.2733 0.047 Uiso 1 1 calc R . . C17 C 0.0761(3) 0.02912(10) -0.1222(2) 0.0321(6) Uani 1 1 d . . . H17A H -0.0111 0.0474 -0.1148 0.048 Uiso 1 1 calc R . . H17B H 0.1012 0.0007 -0.0607 0.048 Uiso 1 1 calc R . . H17C H 0.0529 0.0158 -0.2102 0.048 Uiso 1 1 calc R . . C18 C 0.2017(3) 0.10665(11) 0.4427(3) 0.0388(7) Uani 1 1 d . . . H18A H 0.1442 0.1326 0.4706 0.058 Uiso 1 1 calc R . . H18B H 0.2337 0.0799 0.5085 0.058 Uiso 1 1 calc R . . H18C H 0.1389 0.0916 0.3610 0.058 Uiso 1 1 calc R . . C19 C 0.4212(4) 0.15374(14) 0.5448(3) 0.0561(9) Uani 1 1 d . . . H19A H 0.4533 0.1277 0.6125 0.084 Uiso 1 1 calc R . . H19B H 0.3615 0.1798 0.5700 0.084 Uiso 1 1 calc R . . H19C H 0.5093 0.1698 0.5329 0.084 Uiso 1 1 calc R . . C20 C 0.5706(3) 0.03385(11) 0.3763(3) 0.0455(8) Uani 1 1 d . . . H20A H 0.5290 0.0292 0.2825 0.068 Uiso 1 1 calc R . . H20B H 0.4927 0.0471 0.4086 0.068 Uiso 1 1 calc R . . H20C H 0.6066 0.0009 0.4175 0.068 Uiso 1 1 calc R . . C21 C 0.6996(3) 0.07141(10) 0.4077(3) 0.0331(6) Uani 1 1 d . . . C22 C 0.8122(4) 0.05008(12) 0.3476(4) 0.0693(12) Uani 1 1 d . . . H22A H 0.8991 0.0729 0.3675 0.104 Uiso 1 1 calc R . . H22B H 0.7649 0.0477 0.2537 0.104 Uiso 1 1 calc R . . H22C H 0.8447 0.0160 0.3829 0.104 Uiso 1 1 calc R . . C23 C 0.7713(5) 0.07544(15) 0.5534(3) 0.0899(15) Uani 1 1 d . . . H23A H 0.6996 0.0905 0.5904 0.135 Uiso 1 1 calc R . . H23B H 0.8605 0.0971 0.5739 0.135 Uiso 1 1 calc R . . H23C H 0.7998 0.0413 0.5899 0.135 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr1 0.01900(11) 0.02226(11) 0.02015(12) -0.00160(9) 0.00813(8) -0.00343(9) S1 0.0258(3) 0.0296(3) 0.0257(3) -0.0037(2) 0.0120(3) -0.0093(2) N1 0.0261(10) 0.0236(10) 0.0290(11) -0.0025(8) 0.0115(9) -0.0050(8) N2 0.0256(11) 0.0274(10) 0.0310(12) 0.0006(9) 0.0118(9) 0.0005(8) N3 0.0204(10) 0.0268(10) 0.0272(11) -0.0012(8) 0.0086(9) -0.0011(8) N4 0.0243(10) 0.0226(10) 0.0216(10) -0.0030(8) 0.0109(8) -0.0066(8) N5 0.0240(10) 0.0294(10) 0.0218(10) -0.0020(8) 0.0073(8) -0.0045(8) N6 0.0262(10) 0.0353(11) 0.0256(11) -0.0013(9) 0.0133(9) -0.0022(9) C1 0.0222(12) 0.0270(12) 0.0191(11) 0.0007(9) 0.0078(10) -0.0025(9) C2 0.0347(14) 0.0311(13) 0.0269(13) -0.0017(10) 0.0152(11) -0.0060(11) C3 0.0406(15) 0.0419(15) 0.0330(15) -0.0015(12) 0.0192(13) -0.0153(13) C4 0.0337(15) 0.0518(18) 0.0392(16) -0.0002(13) 0.0226(13) -0.0050(12) C5 0.0343(14) 0.0379(15) 0.0386(16) 0.0010(12) 0.0195(13) 0.0069(11) C6 0.0310(13) 0.0248(12) 0.0326(14) 0.0046(10) 0.0125(11) 0.0016(10) C7 0.0223(11) 0.0203(11) 0.0239(12) -0.0017(9) 0.0087(10) -0.0004(9) C8 0.0345(14) 0.0240(12) 0.0320(14) -0.0033(10) 0.0108(11) -0.0048(10) C9 0.0492(17) 0.0267(13) 0.0344(15) -0.0019(11) 0.0165(13) -0.0093(12) C10 0.0361(15) 0.0354(14) 0.0392(15) -0.0078(12) 0.0182(13) -0.0159(12) C11 0.0252(12) 0.0295(13) 0.0309(14) -0.0074(10) 0.0100(11) -0.0085(10) C12 0.0226(12) 0.0367(14) 0.0405(16) -0.0073(12) 0.0100(12) -0.0065(11) C13 0.0395(15) 0.0274(13) 0.0402(16) -0.0004(11) 0.0134(13) 0.0031(11) C14 0.0415(16) 0.0325(14) 0.0329(15) 0.0060(11) 0.0050(13) 0.0064(12) C15 0.0334(15) 0.0439(16) 0.0527(19) 0.0092(14) 0.0209(14) 0.0091(12) C16 0.0338(14) 0.0370(14) 0.0213(13) 0.0012(11) 0.0056(11) -0.0026(11) C17 0.0255(13) 0.0417(15) 0.0280(14) -0.0106(11) 0.0073(11) -0.0091(11) C18 0.0362(15) 0.0552(18) 0.0316(15) -0.0022(13) 0.0203(13) -0.0070(13) C19 0.054(2) 0.079(2) 0.0453(19) -0.0316(17) 0.0301(17) -0.0313(18) C20 0.0339(15) 0.0360(15) 0.066(2) 0.0201(14) 0.0163(15) 0.0031(12) C21 0.0246(13) 0.0336(14) 0.0372(15) 0.0026(11) 0.0049(11) 0.0048(11) C22 0.050(2) 0.0374(17) 0.140(4) 0.007(2) 0.058(2) 0.0097(15) C23 0.122(4) 0.063(2) 0.044(2) 0.0045(19) -0.028(2) 0.016(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zr1 N6 2.0736(19) . ? Zr1 N3 2.0864(19) . ? Zr1 N1 2.1387(19) . ? Zr1 N4 2.2790(18) . ? Zr1 N2 2.541(2) . ? Zr1 S1 2.7012(6) . ? S1 C7 1.751(2) . ? N1 C11 1.371(3) . ? N1 C8 1.373(3) . ? N2 C15 1.478(3) . ? N2 C14 1.486(3) . ? N2 C13 1.504(3) . ? N3 C12 1.466(3) . ? N3 C21 1.474(3) . ? N4 C7 1.328(3) . ? N4 C1 1.428(3) . ? N5 C7 1.340(3) . ? N5 C16 1.459(3) . ? N5 C17 1.464(3) . ? N6 C18 1.441(3) . ? N6 C19 1.449(3) . ? C1 C2 1.390(3) . ? C1 C6 1.393(3) . ? C2 C3 1.388(3) . ? C3 C4 1.375(4) . ? C4 C5 1.386(4) . ? C5 C6 1.393(3) . ? C8 C9 1.374(3) . ? C8 C13 1.486(4) . ? C9 C10 1.424(4) . ? C10 C11 1.378(3) . ? C11 C12 1.500(4) . ? C20 C21 1.516(4) . ? C21 C23 1.521(4) . ? C21 C22 1.530(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N6 Zr1 N3 104.45(8) . . ? N6 Zr1 N1 109.40(8) . . ? N3 Zr1 N1 73.54(7) . . ? N6 Zr1 N4 148.23(7) . . ? N3 Zr1 N4 94.02(7) . . ? N1 Zr1 N4 100.45(7) . . ? N6 Zr1 N2 91.81(7) . . ? N3 Zr1 N2 142.50(7) . . ? N1 Zr1 N2 69.19(7) . . ? N4 Zr1 N2 88.74(7) . . ? N6 Zr1 S1 86.78(6) . . ? N3 Zr1 S1 127.17(5) . . ? N1 Zr1 S1 150.76(6) . . ? N4 Zr1 S1 61.54(5) . . ? N2 Zr1 S1 86.62(5) . . ? C7 S1 Zr1 79.18(8) . . ? C11 N1 C8 108.19(19) . . ? C11 N1 Zr1 119.24(15) . . ? C8 N1 Zr1 126.97(16) . . ? C15 N2 C14 107.2(2) . . ? C15 N2 C13 109.4(2) . . ? C14 N2 C13 107.48(19) . . ? C15 N2 Zr1 111.87(15) . . ? C14 N2 Zr1 110.91(14) . . ? C13 N2 Zr1 109.79(14) . . ? C12 N3 C21 115.69(19) . . ? C12 N3 Zr1 122.11(15) . . ? C21 N3 Zr1 122.20(15) . . ? C7 N4 C1 125.22(19) . . ? C7 N4 Zr1 105.61(13) . . ? C1 N4 Zr1 128.70(14) . . ? C7 N5 C16 122.60(19) . . ? C7 N5 C17 120.06(19) . . ? C16 N5 C17 115.99(19) . . ? C18 N6 C19 109.2(2) . . ? C18 N6 Zr1 133.74(17) . . ? C19 N6 Zr1 117.02(16) . . ? C2 C1 C6 119.0(2) . . ? C2 C1 N4 118.6(2) . . ? C6 C1 N4 122.2(2) . . ? C3 C2 C1 120.1(2) . . ? C4 C3 C2 121.0(2) . . ? C3 C4 C5 119.4(2) . . ? C4 C5 C6 120.2(2) . . ? C1 C6 C5 120.3(2) . . ? N4 C7 N5 126.8(2) . . ? N4 C7 S1 112.70(17) . . ? N5 C7 S1 120.38(17) . . ? N1 C8 C9 109.1(2) . . ? N1 C8 C13 113.3(2) . . ? C9 C8 C13 137.4(2) . . ? C8 C9 C10 106.8(2) . . ? C11 C10 C9 106.9(2) . . ? N1 C11 C10 109.0(2) . . ? N1 C11 C12 114.5(2) . . ? C10 C11 C12 136.3(2) . . ? N3 C12 C11 107.75(19) . . ? C8 C13 N2 109.4(2) . . ? N3 C21 C20 107.9(2) . . ? N3 C21 C23 111.3(2) . . ? C20 C21 C23 109.3(3) . . ? N3 C21 C22 111.2(2) . . ? C20 C21 C22 106.8(2) . . ? C23 C21 C22 110.2(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.504 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.075 data_ray243_0m _database_code_depnum_ccdc_archive 'CCDC 867479' #TrackingRef '- cpd 8--ray243_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H67 N9 O3 Zr' _chemical_formula_weight 873.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3294(5) _cell_length_b 12.1455(5) _cell_length_c 17.9863(8) _cell_angle_alpha 90.132(2) _cell_angle_beta 96.703(2) _cell_angle_gamma 109.661(2) _cell_volume 2312.43(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max 28.76 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5327 _exptl_absorpt_correction_T_max 0.7738 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 37208 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 28.76 _reflns_number_total 11975 _reflns_number_gt 10367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_cell_refinement 'SAINT V7.68A (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.68A (Bruker AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.6329P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11975 _refine_ls_number_parameters 534 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0433 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0935 _refine_ls_wR_factor_gt 0.0853 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Zr1 Zr 0.412932(14) 0.230155(12) 0.291717(8) 0.01673(5) Uani 1 1 d . . . O1 O 0.24619(11) 0.11825(10) 0.21758(6) 0.0236(2) Uani 1 1 d . . . O2 O 0.40962(11) 0.29401(9) 0.40575(6) 0.0201(2) Uani 1 1 d . . . O3 O 0.48667(11) 0.42259(9) 0.28145(6) 0.0206(2) Uani 1 1 d . . . N1 N 0.34259(13) 0.10439(12) 0.38208(7) 0.0209(3) Uani 1 1 d . . . N2 N 0.32561(13) 0.18653(12) 0.50190(7) 0.0200(3) Uani 1 1 d . . . N3 N 0.05696(14) 0.14733(14) 0.19122(9) 0.0298(3) Uani 1 1 d . . . N4 N 0.22728(13) 0.26478(12) 0.28060(8) 0.0218(3) Uani 1 1 d . . . N5 N 0.46706(14) 0.30967(12) 0.18231(7) 0.0227(3) Uani 1 1 d . . . N6 N 0.51242(15) 0.51692(12) 0.17180(8) 0.0272(3) Uani 1 1 d . . . N7 N 0.63209(13) 0.27956(13) 0.35587(8) 0.0245(3) Uani 1 1 d . . . N8 N 0.49605(13) 0.09909(12) 0.24815(7) 0.0221(3) Uani 1 1 d . . . N9 N 0.31926(17) -0.18618(15) 0.14283(11) 0.0420(4) Uani 1 1 d . . . H9A H 0.3865 -0.2076 0.1461 0.050 Uiso 1 1 calc R . . C1 C 0.19285(19) 0.03830(17) 0.58138(11) 0.0353(4) Uani 1 1 d . . . H1A H 0.1930 -0.0286 0.6117 0.053 Uiso 1 1 calc R . . H1B H 0.1227 0.0132 0.5407 0.053 Uiso 1 1 calc R . . H1C H 0.1828 0.0996 0.6130 0.053 Uiso 1 1 calc R . . C2 C 0.31668(17) 0.08586(15) 0.54861(9) 0.0246(3) Uani 1 1 d . . . H2A H 0.3870 0.1093 0.5901 0.030 Uiso 1 1 calc R . . H2B H 0.3271 0.0227 0.5180 0.030 Uiso 1 1 calc R . . C3 C 0.34204(16) 0.29816(15) 0.54126(9) 0.0238(3) Uani 1 1 d . . . H3A H 0.2852 0.2828 0.5807 0.029 Uiso 1 1 calc R . . H3B H 0.3164 0.3499 0.5052 0.029 Uiso 1 1 calc R . . C4 C 0.47639(18) 0.36135(18) 0.57694(11) 0.0339(4) Uani 1 1 d . . . H4A H 0.4800 0.4324 0.6044 0.051 Uiso 1 1 calc R . . H4B H 0.5325 0.3825 0.5378 0.051 Uiso 1 1 calc R . . H4C H 0.5035 0.3099 0.6117 0.051 Uiso 1 1 calc R . . C5 C 0.63924(18) 0.20304(17) 0.41979(10) 0.0314(4) Uani 1 1 d . . . H5A H 0.7280 0.2167 0.4386 0.047 Uiso 1 1 calc R . . H5B H 0.5980 0.1208 0.4028 0.047 Uiso 1 1 calc R . . H5C H 0.5965 0.2213 0.4600 0.047 Uiso 1 1 calc R . . C6 C 0.69573(17) 0.40137(16) 0.38428(11) 0.0324(4) Uani 1 1 d . . . H6A H 0.7819 0.4113 0.4068 0.049 Uiso 1 1 calc R . . H6B H 0.6489 0.4200 0.4221 0.049 Uiso 1 1 calc R . . H6C H 0.6988 0.4540 0.3428 0.049 Uiso 1 1 calc R . . C7 C 0.69890(16) 0.25208(16) 0.29631(10) 0.0279(4) Uani 1 1 d . . . H7A H 0.7845 0.2551 0.3178 0.034 Uiso 1 1 calc R . . H7B H 0.7079 0.3108 0.2574 0.034 Uiso 1 1 calc R . . C8 C 0.35663(14) 0.19193(14) 0.43116(8) 0.0186(3) Uani 1 1 d . . . C9 C 0.26770(16) -0.01449(14) 0.38405(8) 0.0216(3) Uani 1 1 d . . . C10 C 0.14066(17) -0.05047(15) 0.39455(10) 0.0278(4) Uani 1 1 d . . . H10A H 0.1031 0.0062 0.4046 0.033 Uiso 1 1 calc R . . C11 C 0.06842(18) -0.16843(17) 0.39041(11) 0.0343(4) Uani 1 1 d . . . H11A H -0.0179 -0.1918 0.3983 0.041 Uiso 1 1 calc R . . C12 C 0.12096(19) -0.25247(16) 0.37490(11) 0.0350(4) Uani 1 1 d . . . H12A H 0.0712 -0.3332 0.3718 0.042 Uiso 1 1 calc R . . C13 C 0.2467(2) -0.21725(16) 0.36400(11) 0.0355(4) Uani 1 1 d . . . H13A H 0.2835 -0.2743 0.3534 0.043 Uiso 1 1 calc R . . C14 C 0.31973(18) -0.09986(15) 0.36834(10) 0.0287(4) Uani 1 1 d . . . H14A H 0.4060 -0.0771 0.3606 0.034 Uiso 1 1 calc R . . C15 C 0.32434(18) -0.07550(15) 0.17777(10) 0.0301(4) Uani 1 1 d . . . H15A H 0.2683 -0.0910 0.2177 0.036 Uiso 1 1 calc R . . H15B H 0.2949 -0.0284 0.1399 0.036 Uiso 1 1 calc R . . C16 C 0.45848(17) -0.00904(15) 0.21073(9) 0.0254(3) Uani 1 1 d . . . C17 C 0.56146(19) -0.04228(17) 0.20387(11) 0.0331(4) Uani 1 1 d . . . H17A H 0.5602 -0.1134 0.1811 0.040 Uiso 1 1 calc R . . C18 C 0.66924(19) 0.04890(17) 0.23685(11) 0.0352(4) Uani 1 1 d . . . H18A H 0.7544 0.0512 0.2407 0.042 Uiso 1 1 calc R . . C19 C 0.62672(17) 0.13367(16) 0.26229(10) 0.0275(4) Uani 1 1 d . . . C20 C 0.48798(15) 0.41756(14) 0.20962(9) 0.0205(3) Uani 1 1 d . . . C21 C 0.5584(2) 0.52575(17) 0.09833(10) 0.0387(5) Uani 1 1 d . . . H21A H 0.5647 0.6035 0.0789 0.046 Uiso 1 1 calc R . . H21B H 0.4957 0.4657 0.0632 0.046 Uiso 1 1 calc R . . C22 C 0.5251(2) 0.62649(15) 0.21167(10) 0.0340(4) Uani 1 1 d . . . H22A H 0.4713 0.6082 0.2527 0.041 Uiso 1 1 calc R . . H22B H 0.4930 0.6757 0.1766 0.041 Uiso 1 1 calc R . . C23 C 0.31574(18) 0.27450(16) 0.06898(9) 0.0305(4) Uani 1 1 d . . . H23A H 0.2744 0.3210 0.0902 0.037 Uiso 1 1 calc R . . C24 C 0.42390(17) 0.26335(14) 0.10826(9) 0.0240(3) Uani 1 1 d . . . C25 C 0.4830(2) 0.19399(17) 0.07671(10) 0.0328(4) Uani 1 1 d . . . H25A H 0.5563 0.1843 0.1031 0.039 Uiso 1 1 calc R . . C26 C 0.4339(2) 0.13887(19) 0.00611(11) 0.0408(5) Uani 1 1 d . . . H26A H 0.4751 0.0928 -0.0157 0.049 Uiso 1 1 calc R . . C27 C 0.3263(2) 0.15048(18) -0.03232(11) 0.0398(5) Uani 1 1 d . . . H27A H 0.2930 0.1119 -0.0801 0.048 Uiso 1 1 calc R . . C28 C 0.2673(2) 0.21850(18) -0.00090(10) 0.0372(4) Uani 1 1 d . . . H28A H 0.1934 0.2270 -0.0272 0.045 Uiso 1 1 calc R . . C29 C 0.17255(16) 0.17571(14) 0.23060(9) 0.0229(3) Uani 1 1 d . . . C30 C 0.01244(19) 0.04147(19) 0.14180(12) 0.0396(5) Uani 1 1 d . . . H30A H 0.0844 0.0332 0.1188 0.048 Uiso 1 1 calc R . . H30B H -0.0507 0.0490 0.1010 0.048 Uiso 1 1 calc R . . C31 C -0.01840(18) 0.22554(18) 0.18756(11) 0.0349(4) Uani 1 1 d . . . H31A H -0.0329 0.2422 0.2390 0.042 Uiso 1 1 calc R . . H31B H -0.1018 0.1846 0.1585 0.042 Uiso 1 1 calc R . . C32 C 0.06850(16) 0.23471(15) 0.36729(10) 0.0248(3) Uani 1 1 d . . . H32A H 0.0323 0.1544 0.3516 0.030 Uiso 1 1 calc R . . C33 C 0.16802(15) 0.30830(14) 0.33233(9) 0.0210(3) Uani 1 1 d . . . C34 C 0.21839(16) 0.42606(15) 0.35566(10) 0.0259(3) Uani 1 1 d . . . H34A H 0.2855 0.4776 0.3323 0.031 Uiso 1 1 calc R . . C35 C 0.17100(18) 0.46856(16) 0.41303(10) 0.0293(4) Uani 1 1 d . . . H35A H 0.2058 0.5491 0.4284 0.035 Uiso 1 1 calc R . . C36 C 0.07331(18) 0.39441(17) 0.44806(10) 0.0307(4) Uani 1 1 d . . . H36A H 0.0421 0.4236 0.4877 0.037 Uiso 1 1 calc R . . C37 C 0.02199(17) 0.27795(16) 0.42472(10) 0.0292(4) Uani 1 1 d . . . H37A H -0.0456 0.2270 0.4480 0.035 Uiso 1 1 calc R . . C38 C 0.0431(2) 0.3404(2) 0.15197(13) 0.0465(5) Uani 1 1 d . . . H38A H -0.0118 0.3880 0.1511 0.070 Uiso 1 1 calc R . . H38B H 0.0561 0.3249 0.1006 0.070 Uiso 1 1 calc R . . H38C H 0.1247 0.3826 0.1812 0.070 Uiso 1 1 calc R . . C39 C -0.0455(2) -0.0651(2) 0.18380(14) 0.0481(5) Uani 1 1 d . . . H39A H -0.0740 -0.1342 0.1494 0.072 Uiso 1 1 calc R . . H39B H -0.1178 -0.0577 0.2058 0.072 Uiso 1 1 calc R . . H39C H 0.0173 -0.0733 0.2237 0.072 Uiso 1 1 calc R . . C40 C 0.1466(4) -0.1953(3) 0.04256(19) 0.0934(12) Uani 1 1 d . . . H40A H 0.1335 -0.1280 0.0659 0.140 Uiso 1 1 calc R . . H40B H 0.0660 -0.2478 0.0170 0.140 Uiso 1 1 calc R . . H40C H 0.2069 -0.1679 0.0061 0.140 Uiso 1 1 calc R . . C41 C 0.1029(3) -0.3089(3) 0.15693(19) 0.0748(9) Uani 1 1 d . . . H41A H 0.1349 -0.3551 0.1935 0.112 Uiso 1 1 calc R . . H41B H 0.0227 -0.3588 0.1295 0.112 Uiso 1 1 calc R . . H41C H 0.0896 -0.2440 0.1831 0.112 Uiso 1 1 calc R . . C42 C 0.1983(2) -0.2604(2) 0.10223(14) 0.0487(6) Uani 1 1 d . . . C43 C 0.2243(3) -0.3634(3) 0.0665(2) 0.0804(10) Uani 1 1 d . . . H43A H 0.2537 -0.4071 0.1058 0.121 Uiso 1 1 calc R . . H43B H 0.2893 -0.3336 0.0330 0.121 Uiso 1 1 calc R . . H43C H 0.1464 -0.4152 0.0377 0.121 Uiso 1 1 calc R . . C44 C 0.6588(2) 0.69602(18) 0.24432(12) 0.0446(5) Uani 1 1 d . . . H44A H 0.6596 0.7667 0.2710 0.067 Uiso 1 1 calc R . . H44B H 0.7120 0.7182 0.2039 0.067 Uiso 1 1 calc R . . H44C H 0.6914 0.6483 0.2793 0.067 Uiso 1 1 calc R . . C45 C 0.6848(2) 0.5099(2) 0.09986(14) 0.0555(7) Uani 1 1 d . . . H45A H 0.7102 0.5177 0.0493 0.083 Uiso 1 1 calc R . . H45B H 0.6787 0.4319 0.1172 0.083 Uiso 1 1 calc R . . H45C H 0.7478 0.5696 0.1340 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zr1 0.01868(8) 0.01469(8) 0.01509(7) -0.00034(5) 0.00177(5) 0.00354(6) O1 0.0243(6) 0.0215(6) 0.0224(5) -0.0043(4) 0.0006(5) 0.0051(5) O2 0.0230(6) 0.0174(6) 0.0182(5) 0.0004(4) 0.0026(4) 0.0046(4) O3 0.0251(6) 0.0171(6) 0.0159(5) -0.0004(4) 0.0018(4) 0.0025(5) N1 0.0263(7) 0.0169(7) 0.0186(6) 0.0009(5) 0.0046(5) 0.0054(5) N2 0.0239(7) 0.0201(7) 0.0165(6) 0.0009(5) 0.0031(5) 0.0078(6) N3 0.0232(7) 0.0276(8) 0.0327(8) -0.0068(6) -0.0071(6) 0.0044(6) N4 0.0197(7) 0.0198(7) 0.0240(7) -0.0040(5) -0.0001(5) 0.0052(5) N5 0.0306(7) 0.0193(7) 0.0160(6) -0.0002(5) 0.0043(5) 0.0051(6) N6 0.0393(9) 0.0189(7) 0.0187(6) 0.0022(5) 0.0036(6) 0.0036(6) N7 0.0228(7) 0.0238(7) 0.0254(7) -0.0045(6) -0.0011(6) 0.0076(6) N8 0.0232(7) 0.0192(7) 0.0226(6) -0.0021(5) 0.0044(6) 0.0054(6) N9 0.0369(9) 0.0266(9) 0.0599(11) -0.0193(8) 0.0003(8) 0.0093(7) C1 0.0397(11) 0.0344(11) 0.0318(9) 0.0085(8) 0.0131(8) 0.0095(9) C2 0.0307(9) 0.0258(9) 0.0190(7) 0.0051(6) 0.0031(7) 0.0118(7) C3 0.0295(9) 0.0245(9) 0.0193(7) -0.0019(6) 0.0037(7) 0.0116(7) C4 0.0342(10) 0.0338(11) 0.0299(9) -0.0115(8) -0.0017(8) 0.0088(8) C5 0.0278(9) 0.0398(11) 0.0276(9) 0.0032(8) 0.0001(7) 0.0140(8) C6 0.0233(9) 0.0288(10) 0.0394(10) -0.0125(8) -0.0057(8) 0.0047(7) C7 0.0224(8) 0.0310(10) 0.0299(9) -0.0013(7) 0.0051(7) 0.0078(7) C8 0.0176(7) 0.0198(8) 0.0179(7) 0.0012(6) 0.0010(6) 0.0059(6) C9 0.0294(8) 0.0172(8) 0.0167(7) 0.0018(6) 0.0019(6) 0.0063(7) C10 0.0267(9) 0.0233(9) 0.0338(9) 0.0035(7) 0.0033(7) 0.0092(7) C11 0.0263(9) 0.0274(10) 0.0443(11) 0.0057(8) 0.0026(8) 0.0032(8) C12 0.0380(11) 0.0175(9) 0.0427(11) 0.0026(8) 0.0009(9) 0.0019(8) C13 0.0446(11) 0.0209(9) 0.0447(11) 0.0035(8) 0.0101(9) 0.0145(8) C14 0.0302(9) 0.0234(9) 0.0335(9) 0.0034(7) 0.0073(8) 0.0093(7) C15 0.0343(10) 0.0210(9) 0.0327(9) -0.0081(7) 0.0007(8) 0.0075(7) C16 0.0331(9) 0.0193(8) 0.0233(8) -0.0007(6) 0.0056(7) 0.0077(7) C17 0.0390(11) 0.0258(10) 0.0373(10) -0.0058(8) 0.0084(8) 0.0134(8) C18 0.0316(10) 0.0348(11) 0.0430(11) -0.0049(8) 0.0077(9) 0.0151(9) C19 0.0260(9) 0.0297(10) 0.0277(8) -0.0018(7) 0.0053(7) 0.0102(7) C20 0.0205(8) 0.0193(8) 0.0191(7) 0.0007(6) 0.0021(6) 0.0033(6) C21 0.0601(13) 0.0242(10) 0.0205(8) 0.0027(7) 0.0104(9) -0.0023(9) C22 0.0538(12) 0.0167(9) 0.0269(9) 0.0018(7) 0.0018(8) 0.0071(8) C23 0.0357(10) 0.0315(10) 0.0219(8) -0.0003(7) 0.0040(7) 0.0080(8) C24 0.0324(9) 0.0179(8) 0.0174(7) 0.0007(6) 0.0071(7) 0.0016(7) C25 0.0420(11) 0.0302(10) 0.0261(9) -0.0030(7) 0.0062(8) 0.0115(8) C26 0.0563(14) 0.0354(11) 0.0301(10) -0.0098(8) 0.0104(10) 0.0133(10) C27 0.0508(13) 0.0346(11) 0.0222(8) -0.0072(8) 0.0026(8) -0.0002(9) C28 0.0382(11) 0.0387(11) 0.0259(9) 0.0003(8) 0.0005(8) 0.0026(9) C29 0.0217(8) 0.0199(8) 0.0231(7) 0.0003(6) 0.0007(6) 0.0025(6) C30 0.0314(10) 0.0409(12) 0.0383(11) -0.0152(9) -0.0094(8) 0.0060(9) C31 0.0246(9) 0.0440(12) 0.0345(10) -0.0037(8) -0.0069(8) 0.0132(8) C32 0.0213(8) 0.0201(8) 0.0315(8) 0.0009(7) 0.0006(7) 0.0060(7) C33 0.0183(7) 0.0208(8) 0.0238(7) -0.0002(6) -0.0018(6) 0.0081(6) C34 0.0244(8) 0.0214(8) 0.0302(8) 0.0001(7) 0.0014(7) 0.0063(7) C35 0.0338(10) 0.0211(9) 0.0348(9) -0.0039(7) 0.0004(8) 0.0130(8) C36 0.0306(9) 0.0362(10) 0.0320(9) -0.0012(8) 0.0052(8) 0.0195(8) C37 0.0239(8) 0.0315(10) 0.0331(9) 0.0040(7) 0.0065(7) 0.0097(7) C38 0.0439(12) 0.0471(13) 0.0495(13) 0.0045(10) -0.0056(10) 0.0207(11) C39 0.0461(13) 0.0359(12) 0.0566(14) -0.0101(10) 0.0020(11) 0.0078(10) C40 0.122(3) 0.063(2) 0.069(2) -0.0276(16) -0.044(2) 0.016(2) C41 0.0563(17) 0.0523(17) 0.098(2) -0.0335(16) 0.0181(16) -0.0070(13) C42 0.0462(13) 0.0311(12) 0.0605(14) -0.0229(10) -0.0010(11) 0.0051(10) C43 0.0621(18) 0.0495(17) 0.117(3) -0.0567(17) 0.0077(18) 0.0037(14) C44 0.0595(14) 0.0269(11) 0.0340(10) -0.0042(8) -0.0010(10) -0.0004(10) C45 0.0674(16) 0.0434(14) 0.0502(13) -0.0014(11) 0.0333(13) 0.0030(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zr1 O2 2.1999(11) . ? Zr1 O1 2.2068(12) . ? Zr1 O3 2.2178(11) . ? Zr1 N5 2.2524(12) . ? Zr1 N1 2.2593(12) . ? Zr1 N4 2.2668(13) . ? Zr1 N8 2.2826(13) . ? Zr1 N7 2.4863(14) . ? O1 C29 1.294(2) . ? O2 C8 1.2932(18) . ? O3 C20 1.2954(18) . ? N1 C8 1.336(2) . ? N1 C9 1.410(2) . ? N2 C8 1.3549(18) . ? N2 C2 1.4672(19) . ? N2 C3 1.473(2) . ? N3 C29 1.347(2) . ? N3 C30 1.467(2) . ? N3 C31 1.473(2) . ? N4 C29 1.333(2) . ? N4 C33 1.406(2) . ? N5 C20 1.333(2) . ? N5 C24 1.410(2) . ? N6 C20 1.349(2) . ? N6 C22 1.466(2) . ? N6 C21 1.467(2) . ? N7 C6 1.471(2) . ? N7 C7 1.480(2) . ? N7 C5 1.492(2) . ? N8 C16 1.383(2) . ? N8 C19 1.388(2) . ? N9 C15 1.463(2) . ? N9 C42 1.468(3) . ? N9 H9A 0.8800 . ? C1 C2 1.516(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.517(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C19 1.483(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C9 C10 1.392(2) . ? C9 C14 1.397(2) . ? C10 C11 1.387(3) . ? C10 H10A 0.9500 . ? C11 C12 1.386(3) . ? C11 H11A 0.9500 . ? C12 C13 1.380(3) . ? C12 H12A 0.9500 . ? C13 C14 1.384(3) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.508(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.375(2) . ? C17 C18 1.410(3) . ? C17 H17A 0.9500 . ? C18 C19 1.373(2) . ? C18 H18A 0.9500 . ? C21 C45 1.505(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C44 1.510(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.389(3) . ? C23 C28 1.388(3) . ? C23 H23A 0.9500 . ? C24 C25 1.395(2) . ? C25 C26 1.397(3) . ? C25 H25A 0.9500 . ? C26 C27 1.379(3) . ? C26 H26A 0.9500 . ? C27 C28 1.380(3) . ? C27 H27A 0.9500 . ? C28 H28A 0.9500 . ? C30 C39 1.491(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C38 1.515(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C37 1.390(2) . ? C32 C33 1.398(2) . ? C32 H32A 0.9500 . ? C33 C34 1.393(2) . ? C34 C35 1.390(2) . ? C34 H34A 0.9500 . ? C35 C36 1.388(3) . ? C35 H35A 0.9500 . ? C36 C37 1.379(3) . ? C36 H36A 0.9500 . ? C37 H37A 0.9500 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 C42 1.513(4) . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C42 1.519(4) . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 C43 1.533(3) . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Zr1 O1 125.04(4) . . ? O2 Zr1 O3 78.14(4) . . ? O1 Zr1 O3 121.33(4) . . ? O2 Zr1 N5 136.84(5) . . ? O1 Zr1 N5 81.84(5) . . ? O3 Zr1 N5 58.70(4) . . ? O2 Zr1 N1 58.87(4) . . ? O1 Zr1 N1 86.39(5) . . ? O3 Zr1 N1 137.01(4) . . ? N5 Zr1 N1 164.26(5) . . ? O2 Zr1 N4 77.84(4) . . ? O1 Zr1 N4 58.64(5) . . ? O3 Zr1 N4 81.14(5) . . ? N5 Zr1 N4 94.04(5) . . ? N1 Zr1 N4 88.67(5) . . ? O2 Zr1 N8 132.04(4) . . ? O1 Zr1 N8 80.69(5) . . ? O3 Zr1 N8 126.09(4) . . ? N5 Zr1 N8 80.24(5) . . ? N1 Zr1 N8 87.59(5) . . ? N4 Zr1 N8 139.32(5) . . ? O2 Zr1 N7 74.04(4) . . ? O1 Zr1 N7 152.83(5) . . ? O3 Zr1 N7 78.73(4) . . ? N5 Zr1 N7 96.26(5) . . ? N1 Zr1 N7 89.44(5) . . ? N4 Zr1 N7 148.14(5) . . ? N8 Zr1 N7 72.31(5) . . ? C29 O1 Zr1 96.07(10) . . ? C8 O2 Zr1 95.85(9) . . ? C20 O3 Zr1 94.93(9) . . ? C8 N1 C9 128.33(13) . . ? C8 N1 Zr1 91.93(9) . . ? C9 N1 Zr1 135.85(10) . . ? C8 N2 C2 123.29(13) . . ? C8 N2 C3 117.08(13) . . ? C2 N2 C3 116.66(12) . . ? C29 N3 C30 118.02(15) . . ? C29 N3 C31 122.91(16) . . ? C30 N3 C31 118.51(15) . . ? C29 N4 C33 126.91(14) . . ? C29 N4 Zr1 92.21(10) . . ? C33 N4 Zr1 131.90(11) . . ? C20 N5 C24 128.79(14) . . ? C20 N5 Zr1 92.31(9) . . ? C24 N5 Zr1 129.87(11) . . ? C20 N6 C22 119.18(13) . . ? C20 N6 C21 121.68(15) . . ? C22 N6 C21 117.29(14) . . ? C6 N7 C7 109.94(14) . . ? C6 N7 C5 107.19(14) . . ? C7 N7 C5 108.68(13) . . ? C6 N7 Zr1 116.58(10) . . ? C7 N7 Zr1 102.24(10) . . ? C5 N7 Zr1 111.96(11) . . ? C16 N8 C19 105.36(14) . . ? C16 N8 Zr1 140.50(11) . . ? C19 N8 Zr1 114.13(11) . . ? C15 N9 C42 117.87(16) . . ? C15 N9 H9A 121.1 . . ? C42 N9 H9A 121.1 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 C1 113.69(14) . . ? N2 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? N2 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N2 C3 C4 113.55(14) . . ? N2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N7 C5 H5A 109.5 . . ? N7 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N7 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N7 C6 H6A 109.5 . . ? N7 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N7 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N7 C7 C19 109.67(14) . . ? N7 C7 H7A 109.7 . . ? C19 C7 H7A 109.7 . . ? N7 C7 H7B 109.7 . . ? C19 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O2 C8 N1 112.98(13) . . ? O2 C8 N2 118.11(14) . . ? N1 C8 N2 128.89(14) . . ? C10 C9 C14 118.37(15) . . ? C10 C9 N1 122.68(14) . . ? C14 C9 N1 118.70(15) . . ? C11 C10 C9 120.56(16) . . ? C11 C10 H10A 119.7 . . ? C9 C10 H10A 119.7 . . ? C12 C11 C10 120.63(17) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C13 C12 C11 119.06(17) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C12 C13 C14 120.79(17) . . ? C12 C13 H13A 119.6 . . ? C14 C13 H13A 119.6 . . ? C13 C14 C9 120.59(17) . . ? C13 C14 H14A 119.7 . . ? C9 C14 H14A 119.7 . . ? N9 C15 C16 109.14(15) . . ? N9 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? N9 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C17 C16 N8 110.28(16) . . ? C17 C16 C15 125.55(16) . . ? N8 C16 C15 124.03(15) . . ? C16 C17 C18 107.20(16) . . ? C16 C17 H17A 126.4 . . ? C18 C17 H17A 126.4 . . ? C19 C18 C17 106.37(17) . . ? C19 C18 H18A 126.8 . . ? C17 C18 H18A 126.8 . . ? C18 C19 N8 110.75(17) . . ? C18 C19 C7 129.85(17) . . ? N8 C19 C7 119.29(15) . . ? O3 C20 N5 112.98(13) . . ? O3 C20 N6 119.33(15) . . ? N5 C20 N6 127.67(14) . . ? N6 C21 C45 113.75(17) . . ? N6 C21 H21A 108.8 . . ? C45 C21 H21A 108.8 . . ? N6 C21 H21B 108.8 . . ? C45 C21 H21B 108.8 . . ? H21A C21 H21B 107.7 . . ? N6 C22 C44 114.09(17) . . ? N6 C22 H22A 108.7 . . ? C44 C22 H22A 108.7 . . ? N6 C22 H22B 108.7 . . ? C44 C22 H22B 108.7 . . ? H22A C22 H22B 107.6 . . ? C24 C23 C28 120.78(18) . . ? C24 C23 H23A 119.6 . . ? C28 C23 H23A 119.6 . . ? C23 C24 C25 118.97(16) . . ? C23 C24 N5 121.49(15) . . ? C25 C24 N5 119.16(16) . . ? C24 C25 C26 119.66(19) . . ? C24 C25 H25A 120.2 . . ? C26 C25 H25A 120.2 . . ? C27 C26 C25 120.82(19) . . ? C27 C26 H26A 119.6 . . ? C25 C26 H26A 119.6 . . ? C26 C27 C28 119.52(18) . . ? C26 C27 H27A 120.2 . . ? C28 C27 H27A 120.2 . . ? C27 C28 C23 120.2(2) . . ? C27 C28 H28A 119.9 . . ? C23 C28 H28A 119.9 . . ? O1 C29 N4 113.03(15) . . ? O1 C29 N3 119.75(16) . . ? N4 C29 N3 127.06(16) . . ? N3 C30 C39 111.33(18) . . ? N3 C30 H30A 109.4 . . ? C39 C30 H30A 109.4 . . ? N3 C30 H30B 109.4 . . ? C39 C30 H30B 109.4 . . ? H30A C30 H30B 108.0 . . ? N3 C31 C38 113.62(16) . . ? N3 C31 H31A 108.8 . . ? C38 C31 H31A 108.8 . . ? N3 C31 H31B 108.8 . . ? C38 C31 H31B 108.8 . . ? H31A C31 H31B 107.7 . . ? C37 C32 C33 120.66(16) . . ? C37 C32 H32A 119.7 . . ? C33 C32 H32A 119.7 . . ? C34 C33 C32 118.58(15) . . ? C34 C33 N4 119.09(14) . . ? C32 C33 N4 121.96(15) . . ? C35 C34 C33 120.33(16) . . ? C35 C34 H34A 119.8 . . ? C33 C34 H34A 119.8 . . ? C36 C35 C34 120.63(17) . . ? C36 C35 H35A 119.7 . . ? C34 C35 H35A 119.7 . . ? C37 C36 C35 119.39(16) . . ? C37 C36 H36A 120.3 . . ? C35 C36 H36A 120.3 . . ? C36 C37 C32 120.41(16) . . ? C36 C37 H37A 119.8 . . ? C32 C37 H37A 119.8 . . ? C31 C38 H38A 109.5 . . ? C31 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C31 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C30 C39 H39A 109.5 . . ? C30 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C30 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C42 C40 H40A 109.5 . . ? C42 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C42 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 H41A 109.5 . . ? C42 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C42 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N9 C42 C40 112.1(2) . . ? N9 C42 C41 109.9(2) . . ? C40 C42 C41 110.0(3) . . ? N9 C42 C43 106.2(2) . . ? C40 C42 C43 110.3(3) . . ? C41 C42 C43 108.1(2) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C22 C44 H44A 109.5 . . ? C22 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C22 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C21 C45 H45A 109.5 . . ? C21 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C21 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.76 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.791 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.067